Chmical



UNITED STATES PATENT OFFICE.

ALPI-ION'S GAMS, OF BASEL, SWITZERLAND, ASSIGNOR TO SOCIETY OF CHEMICALINDUSTRY IN BASLE, 0F BASEL, SWITZERLAND.

ALLYLES'IER OF THE 2-PIIENYLQ'UINOLIN-4-CARBOXYLIC ACID.

No Drawing.

To all whom it may concern Be it known that I, ALPHONS GAMS, a citizenof the Swiss Republic, and resident of Basel, Switzerland, have inventeda new and useful Allylester of the Q-Phenylquinolin--Carboxylic Acid, ofwhich the following is a full, clear, and exact specification.

It is known that by the action of alkylhalids on the salts ofQ-phenylquinolinlcarboxylic acid alkylesters of this acid are obtained,which possess certain advantages over the free acid, namely theadvantage of tastelessness.

I have now found, that the same advantages belong to the allylester ofthe said 2- phenylquinolimt-carboxylic acid, which has over thealkylesters the further advantage to dissolve the uric acid more easilythan the said acid itself, while the introduction of an alkyl group inthe said acid does not increase the specific dissolving action of thisacid on uric acid.

All known methods for the esterification of acids can be employed forthe preparation of the new allylester. For instance a salt ofthe Q-henylquinOlin- L-carboxylic acid can be decomposed by an allylhalid in aconvenient solvent or gaseous dry hydrochloric acid can be introducedinto an allylalcoholic solution of the 2-phenylquinolinl-carboxylicacid, or this latter solution can be heated with a little quantity ofconcentrated sulfuric acid or the ohlorid of2-phenylquinolin-4;-carboxylic acid can be brought to react withallylalcohol, etc.

The allylester of 2-phenylquinolin-a r-carboxylic acid is entirelytasteless, boils an cacao (under a pressure of 15 nun. of mercury) at260 C. and melt-s at 30 C. It crystallizes from alcohol in long needles,is insoluble in water, readily soluble in alcohol, ether, acetone andoils. Its hydrochlorid constitutes, when recrystallized from strongalcohol, small citron-yellow needles melting at 145 to 1&7" C., whichare insoluble in ether and readily soluble in hot alcohol. By addingwater to the said hydrochlorid, it is instantaneously split into theester and hydrochloric acid. The hydrochlorid possesses a weakly sweettaste.

Example 1. 100 gr. of sodium Q-PlIQHYlCllllXlOllIl-l-Gfif- Specificationof Letters Patent.

until saturation.

Patented Apr. 13, 1920.

Application filed May 29, 1919. Serial No. 300,659.

boxylate are dissolved injO 0. cm. of acetone, heated to boiling, on thewater-bath, in a receptacle provided with a reflux cooler and hereafter50 gr. allylbromid (or an equivalent quantity of allylchlorid) are addedthereto. The reaction being completed, that is to say, after about 6hours, the acetone and the allylating agent still present are distilledolf. The residue is dissolved in a separating funnel and the resultingsolution in ether is washed first with a dilute solution of sodiumcarbonate and afterward with water and finally dried over calciumchlorid.

If alcoholic hydrogen chlorid is added to the dry solution in ether, thehydrochlorid of the new allyl ester is precipitated intthe form of ayellow crystalline precipi- For its purification the free ester isdistilled in mono. Hereby the ester distils at 260 under a pressure of15 111.111. of mercury and is collected in the form of a weaklyyellowish oil, from which, after cooling with ice, feebly yellowishcolored needles separate.

E mamplc 2.

250 gr. of 2-phenylquinolinl-carboxylic acid are dissolved in an excessof allylalcohol, the solution obtained is heated to boiling in arecipient provided with a refiuX cooler and afterward gaseous hydrogenchlorid is introduced into the said solution distilled off on a waterbath under a -reduced pressure and the residue is extracted 1 withether. In order to separate the hydrogen chlorid and the2-phenylquinolin-eicarboxylic acid in excess, the solution in ether iswashed first with a solution of sodium carbonate and afterward withwater. After the ether has been distilled off, the ester remains as athick oil which concretes on ice.

Example 3.

2'70 gr. of chlorid of Q-phenylquinolin-etcarboxylic acid are dissolvedin benzene and heated with an excess of allylalcohol on the water bath,until no more hydrochloric acid escapes. The reaction being achieved,the benzene and the allylalc-ohol Hereafter the alcohol is are distilledoff in vacuo and the residue is tuting, when recrystallized from strongalpoured into water. The further isolation coho, small citron-yellowneedles melting of the ester is effected as in Example 2. at 145 to 147(1, insoluble in ether and What I claim is: readily soluble inhotalcohol, being in- 5 As a new article of manufacture theherestantaneously split into the ester and hy- 20 in describedallylester of 2-phenylquinolindrogen chlorid, when 1t comes into contactel-carboxylic acid, which dissolves uric acid with water, and possessinga weakly sweet more easily than the Q-phenylquinolin-ltaste.

carboxylic acid and its alkyl esters, is en- In witness whereofIhavehereunto signed 10 tirely tasteless, boils in oacuo (under a presmy namethis 30th day of April, 1919, in 25 sure of 15 mm. of mercury) at 2600., the presence of two subscribing witnesses.

melts at 30 G., crystallizes from alcohol DR. ALPHOLS GAMS. in longneedles, is insoluble in water, Witnesses: readily soluble in alcohol,ether, acetone Soo'rr TAGGART,

15 and oils and forms a hydrochlorid consti- AMAND BEAME.

